Best known as the personal secretary to President George Washington serving under the President from 1784 until Washington's death in 1799. It is through Lear's personal journal that we receive the account of Washington's final moments before death and his last words: "'Tis well."
Prior to working for Washington, Lear served as President Thomas Jefferson's envoy to Saint-Domingue and as peace envoy in the Mediterranean during the Barbary Wars. Lear was responsible for negotiating a peace that would end the first Barbary War. Instead of joining the Continental Army, Lear attended Harvard College during the Revolutionary War later graduating in 1783. His career began as a teacher until he was recommended for the combined job of tutoring Martha Washington's grandchildren and acting as George Washington's personal secretary. Residing in Washington's house, Lear's status quickly elevated beyond secretary to Washington's right hand man. Lear's friendship with Washington continued during Washington's presidency as the two would often dine alone together. In 1799, Washington unexpectedly died while Lear was visiting him in Mount Vernon. It is Lear's famous diary entry that describes Washington's final hours and details the President's last words, "Tis well."

Lear would commit suicide by pistol on October 11, 1816. The reasons for his suicide are unknown.

This manuscript letter, dated September 18, 1816, was written less than one month prior to Lear's suicide. Addressed to Colonel Jessup at New Orleans, the letter was written by Lear in his role as accountant for the War Department. It concerns the payment of troops and mentions General Andrew Jackson, whose famous victory at the Battle of New Orleans the previous year was the high point of the War of 1812. It is signed "Tobias Lear." $1200.00